What Happens When You Swap Galas for Personal Connection
Jenny Love
Published: 12/30/2025

When Matthew Roberts, Vice President of Philanthropy at Vail Health Foundation, stood in front of a room full of healthcare fundraisers at the 2025 AHP International Conference, he knew what everyone was thinking. Sure, Vail Health Foundation is an AHP High Performer. But it's based in Vail, Colorado, home to breathtaking mountains and, yes, more than a little affluence. What could other small foundations learn from their success?
But while Vail Health Foundation has raised transformational sums, their success didn’t come from wealth alone. It came from a deliberate shift in mindset: away from special events and transactional fundraising, and toward long-term, one-on-one donor relationships.
Their philosophy can be summed up in two words: think big. Or, as Matthew put it, think of major gifts as “rocket fuel” for the organization.
Moving Beyond Galas into New Galaxies
That “rocket fuel” wasn’t always there. As Matthew and his colleague Dan Pennington, president of the foundation, explained, the foundation once relied heavily on events and annual campaigns. It was a common story: full calendars, overworked staff, and a fundraising strategy that revolved around dinners, silent auctions, and table assignments.
“We grossed about $300,000 on the family dinner-dance that was scheduled for December 28th for 50 years,” Dan recalled. The event was extraordinarily resource-intensive, but the CEO at the time loved it, and it took two years to get it pulled.
The team recognized that while events like the dinner-dance built visibility, they rarely built the kind of deep, transformational giving that sustains a mission. So, they replaced the annual gala circuit with something smaller and infinitely more strategic: intimate gatherings and personal conversations.
“We started doing a lot of salon events, which are 12 people around a dinner table at a benefactor’s or board member’s home,” Matthew said. “We invite those individuals to come and talk about a single topic related to something going on in the health system.”
The smaller scale created space for genuine dialogue, and often, for generosity that far exceeded what a table sponsorship could ever produce.
Campaigns of One
For Matthew and his team, this reorientation toward major gifts came with a powerful concept they call “campaigns of one.”
“We did away with the case-for-support document in our last campaign,” Matthew said. “We just weren't using them, and it was a lot of work to pull that material together. We replaced it with bespoke individual pieces that we could tailor [to a potential benefactor’s interests] as we're walking out the door for a meeting.”
That shift was philosophical. Instead of treating donors as part of a broad appeal or a mass campaign, each relationship became its own, custom-built initiative.
“When you treat [each potential benefactor] as a campaign, from the materials and the conversations to the interactions they have with leadership, it allows you to really focus in on that relationship and give it the time and due diligence it needs,” Matthew explained.
This approach requires patience.
“If we can get a $50,000 gift tomorrow, there's a knee-jerk response to just get the gift,” Matthew said. “But we know if we spend 12 more months with that individual, we will likely get a larger, more meaningful gift.”
Thinking Bigger Than the Organization
One reason this model worked so well for Vail Health is that they refused to think of philanthropy as something that served only their own institution. The foundation’s groundbreaking behavioral health campaign grew into a coalition of over 30 nonprofits across the Vail Valley.
“We partnered with a number of nonprofits in our area to support a big idea,” Roberts said. “Which in turn realized a number of major and principal gifts for our most recent campaign.”
That willingness to look beyond the hospital’s walls created new relationships and new trust within the community. Many of their most generous supporters hadn’t previously donated to Vail Health at all.
It also reinforced a simple truth about fundraising in healthcare: donors—or benefactors, as Vail calls them—want to see the ripple effect of their giving. They don’t give to a hospital; they give to heal a community.
The Payoff of Patience
For small foundations, the idea of a “campaign of one” can feel daunting. It means investing more time per donor, crafting individualized materials, and resisting the urge to chase quick wins. But as Vail Health’s experience shows, that investment pays off in both dollars and relationships by allowing gift officers to work with purpose and creativity and to design giving experiences that reflect what makes each donor unique.
That approach, Matthew emphasized, doesn’t require a big team or deep pockets. It requires intentionality.
Back to the Table
And so we return to that room at the AHP International Conference, where Matthew stood in front of his peers, many of them from much smaller foundations, and dared them to think differently.
“Hopefully, the ideas here around how we've been able to transition to focus on major gifts doesn't get lost in, ‘well, of course you can do that, you’re in Vail,’” Matthew said.
The truth is, you don’t have to be in Vail to adopt their mindset. Whether you serve a community hospital or a regional health system, you can build your own campaigns of one that are focused, personal, and deeply human.